I need to get proficient at that too.
It is important to be completely focused on the prayer the whole time you devote to this. If he is in a bad way, how much sadness and grief can you feel while you pray? By all means, have sadness, grief and tears! End the prayer with praise and thanksgiving! Then feel joyful release that you have opened your heart to God on the person's behalf. Remember, Jesus ate with tax collectors (who were hated above all others) and sinners.
9 To some who were confident of their own righteousness and looked down on everyone else, Jesus told this parable: 10 “Two men went up to the temple to pray, one a Pharisee and the other a tax collector. 11 The Pharisee stood by himself and prayed: ‘God, I thank you that I am not like other people—robbers, evildoers, adulterers—or even like this tax collector. 12 I fast twice a week and give a tenth of all I get.’
13 “But the tax collector stood at a distance. He would not even look up to heaven, but beat his breast and said, ‘God, have mercy on me, a sinner.’
14 “I tell you that this man, rather than the other, went home justified before God. For all those who exalt themselves will be humbled, and those who humble themselves will be exalted.” Luke 18:9-14 NIV